An Informative Guide to St. Martin, St. Barts, and Anguilla
The Leeward Islands by yacht offers one of the most breathtaking and diverse luxury yacht charter Caribbean experiences. With a blend of French refinement, Dutch vibrance, and laid-back island charm, this region is a paradise for travelers seeking adventure, ultimate relaxation, and immersive culture. Whether aboard a sleek superyacht, modern motor yacht, or a spacious crewed catamaran charter, St. Martin, St. Barts, and Anguilla are among the top Caribbean yacht destinations known for calm anchorages, turquoise waters, and extraordinary cuisine.
Why Choose the Leeward Islands for a Yacht Charter
The Leeward Islands are uniquely suited for effortless cruising. Short distances between islands maximize your time swimming, snorkeling, and exploring new shores. Calm waters and protective reefs create ideal conditions for first-time charter guests and seasoned sailors alike.
Each island offers its own identity, St. Martin blends European elegance with Caribbean culture, St. Barts delivers haute-luxury and world-class dining, while Anguilla features pristine beaches and relaxed island charm.
St. Martin’s Princess Juliana Airport provides easy international access, and the region’s excellent marina infrastructure makes embarking on your Caribbean yacht charter seamless. Warm weather, steady trade winds, and abundant sunshine make the Leewards one of the best Caribbean yacht charter regions from December through May. (Check the weather here)
Cultural diversity enriches every stop, French markets, Dutch cafés, Caribbean festivals, gourmet dining, designer boutiques, and artisan crafts form the backdrop of your island-hopping adventure.
Motoring and Sailing
Your vessel sets the tone for your vacation.
Motor yachts deliver speed, luxury, and glamorous onboard amenities, perfect for travelers who want to visit multiple islands expeditiously.
Sailing catamarans offer wide decks, stability, and easy cruising powered by the Caribbean trade winds, ideal for families and groups seeking a relaxing, quiet, island-hopping yacht vacation.
Both options include professional crews who manage itineraries, dining, activities, and water toys, ensuring a premium private yacht rental experience.
Choosing Your Yacht: Catamaran or Motor Yacht
| Feature | Catamaran | Motor Yacht |
|---|---|---|
| Space | Wide, open layout ideal for groups and families | Sleek design with luxurious interiors |
| Speed | Relaxed passages under sail | Fast, efficient island-hopping |
| Access | Shallow draft for close beach anchoring | Requires deeper anchorages |
| Experience | Calm, stable sailing | High-end, glamorous motoring |
Catamarans offer unmatched comfort and stability, perfect for leisurely Caribbean cruising. Motor yachts appeal to travelers who prioritize luxury, speed, and premium styling.
Activities: Snorkeling, Diving, Shopping & Beach Exploration
The Leewards offer world-class snorkeling and diving, making them one of the best Caribbean snorkeling hotspots. Explore Creole Rock in St. Martin, Colombier Bay in St. Barts, and Anguilla’s Shoal Bay East for vibrant reefs and abundant marine life. Water activities include paddleboarding, kayaking, tubing, wakeboarding, and jet skiing (where permitted). White-sand beaches like Orient Bay, Shell Beach, and Rendezvous Bay deliver everything from luxury beach clubs to peaceful, secluded shores.
Enjoy duty-free shopping in Philipsburg, designer boutiques in Gustavia, and local artisan markets in Anguilla. Cultural highlights include historic Fort Louis, island festivals, waterfront cafés, and music-filled Caribbean nights.
Dining Onboard and Ashore
The Enjoyment of Your Private Chef Onboard
Your onboard chef transforms every meal into a personalized dining experience. Fresh Caribbean lobster, tropical fruits, gourmet pastries, artisanal breads, and global cuisine come together in beautifully crafted menus tailored just for you.
Enjoy champagne breakfasts, sunset dinners, beach barbecues, and multi-course culinary creations, each moment designed to elevate your luxury yacht charter Caribbean experience.
Dining Ashore: Top Recommendations
| St. Martin | St. Barts | Anguilla |
|---|
Refined 8-Day, 7-Night Luxury Yacht Charter Itinerary
Day 1: Embark St. Martin (Simpson Bay Lagoon)
Board your yacht, meet the crew, and enjoy a gourmet welcome dinner.
Day 2: Grand Case & Orient Bay
Boutique shopping, fine dining, and fun water sports in two iconic locations.
Day 3: Snorkeling & Beaches
Explore Creole Rock or Tintamarre Island; enjoy dinner onboard or ashore.
Day 4: St. Barts – Gustavia
Designer boutiques, Shell Beach, and dinner at Bagatelle.
Day 5: Beaches & Diving in St. Barts
Visit Colombier Bay or Saline Beach; enjoy a beach club or onboard dining.
Day 6: Anguilla – Rendezvous Bay
Snorkel, paddleboard, relax, and enjoy a sunset barbecue or seaside dinner.
Day 7: Sandy Island & Shoal Bay East
Explore Sandy Cay Islands, vibrant beaches, and enjoy a farewell feast.
Day 8: Return to St. Martin (Marigot)
Enjoy breakfast and a smooth disembarkation.
Final Thoughts
A Leeward Islands luxury yacht charter offers turquoise waters, gourmet cuisine, exclusive beaches, and rich cultural experiences. Whether you seek adventure, tranquility, nightlife, or refined indulgence, this region delivers a world-class Caribbean sailing vacation filled with unforgettable moments, personalized service, and breathtaking scenery.
Ask Us About Yachts and Catamarans Available in the Leeward Islands
Contact Out of the Blue Yacht Charters
Renee Sawyer
Owner Broker
renee@outoftheblueyachtcharters.com
757-759-8960
